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  1. $3,278 to $8,050/night

    Beach Castle

    7 BedroomsBathroomsSleeps 18
    3 nights minstay
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  3. $3,221 to $5,085/night

    Turtle Cove

    3 Bedrooms3.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  5. $3,035 to $11,599/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $2,958 to $11,436/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $2,662 to $8,312/night

    Domus Pacis | 2590 E County Highway 30A

    7 BedroomsBathroomsSleeps 20
    3 nights minstay
    Pool
    FREE CANCELLATION
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  11. $2,532 to $10,410/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $2,130 to $4,969/night

    Buckeye On the Beach | 2288 E Co Hwy 30a

    4 Bedrooms4.5 BathroomsSleeps 10
    3 nights minstay
    Pool
    FREE CANCELLATION
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  15. $2,130 to $3,490/night

    108 Tidal Bridge Way

    5 Bedrooms5.5 BathroomsSleeps 12
    3 nights minstay
    Pool
    FREE CANCELLATION
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  17. $2,072 to $8,530/night

    3902 Pacific Zen

    6 Bedrooms7.5 BathroomsSleeps 14
    2 nights minstay
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  19. $1,846 to $6,200/night

    Halama Hale Private Home

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
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  21. $1,836 to $5,080/night

    Curious Tides- 3132/3134 Estero Blvd- 20% off April + Ma...

    10 BedroomsBathroomsSleeps 20
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $1,725 to $5,693/night

    Dream On

    4 Bedrooms4.5 BathroomsSleeps 14
    2 nights minstay
    Pool
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  25. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
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  27. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
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  29. $1,544 to $3,556/night

    The Good Stuff | 1938 Co Hwy 30A

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pool
    FREE CANCELLATION
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  31. $1,356 to $2,543/night

    Haena Beach House

    2 Bedrooms1.5  BathroomSleeps 4
    3 nights minstay
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  33. $1,349 to $1,609/night

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
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  35. $1,243 to $3,121/night

    Bond House

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
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  37. $1,220 to $4,137/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $1,212 to $4,529/night

    Wailea Elua 1603

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $1,183 to $3,402/night

    Sea Dream | 1960 E Co Hwy 30A

    4 Bedrooms4.5 BathroomsSleeps 12
    3 nights minstay
    Pool
    FREE CANCELLATION
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  43. $1,154 to $5,681/night

    Wailea Beach Villa M312

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  45. $1,124 to $3,100/night

    Second Sandbar | 1946 E. Co Hwy 30A

    3 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
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  47. $1,096 to $5,100/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  49. $1,065 to $5,265/night

    Summer of 42 | 299 Pompano Street

    6 BedroomsBathroomsSleeps 16
    3 nights minstay
    Pool
    FREE CANCELLATION
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  51. $1,065 to $3,674/night

    Outside the Box | 2112 E Co Hwy 30A

    4 Bedrooms6.5 BathroomsSleeps 12
    3 nights minstay
    Pool
    FREE CANCELLATION
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  53. $1,060 to $1,637/night

    JEKYLL HOUSE

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool
    FREE CANCELLATION
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  55. $1,049 to $1,752/night

    Makana Akua Haena

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $1,038 to $3,868/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  59. $1,020 to $3,185/night

    Sunset Tides- 3134 Estero Blvd 20% Off April + May!

    5 Bedrooms4.5 BathroomsSleeps 12
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $1,020 to $3,835/night

    Dog Friendly Oceanfront Beach House

    4 BedroomsBathroomsSleeps 12
    2 nights minstay
    Pets OK
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  63. $1,020 to $2,339/night

    Coastal Tides- 3132 Estero Blvd- 20% off April + May!

    5 Bedrooms4.5 BathroomsSleeps 12
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $1,017 to $3,139/night

    Anahola Aloha Beach House

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Hot Tub
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  67. $1,006 to $3,059/night

    Shellstone Cottage | 8690 E Co Hwy 30A

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool
    FREE CANCELLATION
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  69. $995 to $2,166/night

    Alexander 807

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
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  71. $991 to $2,255/night

    Hale Kalani

    2 Bedrooms1.5  BathroomSleeps 4
    3 nights minstay
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  73. $990 to $3,640/night

    Forever Sunshine- Beach Vacation Rental

    9 BedroomsBathroomsSleeps 26
    1 night minstay
    Pool Pets OK
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $989 to $2,899/night

    Honua Kai Konea 250

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $954 to $4,035/night

    Rum Point Club Resort- 4 Bedroom Luxe Penthouse

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $947 to $2,958/night

    Bella Vita | 2132 E Co Hwy 30A

    4 Bedrooms4.5 BathroomsSleeps 9
    3 nights minstay
    Pool
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $947 to $4,721/night

    PLANTATION HOUSE on Palma Sola Bay Private Pool And Boat...

    7 BedroomsBathroomsSleeps 19
    2 nights minstay
    Pool Hot Tub
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $942 to $1,054/night

    Sea Turtle Ranch

    4 BedroomsBathroomsSleeps 8
    29 nights minstay
    Hot Tub
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $936 to $1,411/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $923 to $2,732/night

    Polo Beach Club 106

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $923 to $2,535/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $918 to $2,307/night

    Hanalei Beachfront Cottage

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Hot Tub
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $906 to $3,732/night

    Nifty Shades of Gray

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $900 to $2,500/night

    Radwood Beach House 1 by Barbados Sotheby's Interna...

    3 Bedrooms3.5 BathroomsSleeps 6
    1 night minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $898 to $2,525/night

    Niulani Lanikai- Kauai Beach House

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $896 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $874 to $2,897/night

    Island Girl- 30 Gulf Beach Road

    5 Bedrooms3.5 BathroomsSleeps 10
    1 night minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $832 to $1,544/night

    Alexander 1003

    4 BedroomsBathroomsSleeps 11
    2 nights minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $832 to $1,544/night

    Alexander 702

    4 BedroomsBathroomsSleeps 9
    2 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $832 to $1,544/night

    Alexander 518

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $832 to $1,544/night

    Alexander 1103

    4 BedroomsBathroomsSleeps 11
    2 nights minstay
    Pool Hot Tub
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $821 to $938/night

    Luxury beachfront home with pool in Islamorada

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $808 to $2,967/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $798 to $2,041/night

    Ocean Ave Spacious Seaside Cottage

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $789 to $4,141/night

    NEW Bay Dreamin 4 Bedroom Private Pool Spa Beach Front P...

    4 Bedrooms3.5 BathroomsSleeps 8
    3 nights minstay
    Pool
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $784 to $3,322/night

    1002 E. Oceanfront

    7 BedroomsBathroomsSleeps 20
    2 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $767 to $2,967/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $756 to $2,735/night

    1011 N. Bayfront A & B

    5 Bedrooms5.5 BathroomsSleeps 12
    2 nights minstay
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $752 to $2,214/night

    Spotted Sandpiper Condo Easy access to Pier, Pool and Be...

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $750 to $3,959/night

    Wailea Beach Villa I204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $735 to $1,424/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $721 to $1,389/night

    Alexander 1001

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $721 to $1,389/night

    Alexander 519

    4 BedroomsBathroomsSleeps 11
    2 nights minstay
    Pool Hot Tub
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $721 to $1,389/night

    Alexander 1420

    4 BedroomsBathroomsSleeps 11
    2 nights minstay
    Pool Hot Tub
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $721 to $1,389/night

    Alexander 1401

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $721 to $2,337/night

    Noelani 306

    Multiple Units Available
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $721 to $1,389/night

    Alexander 1701

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $721 to $1,389/night

    Alexander 802

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    Pool Hot Tub
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $711 to $1,172/night

    1386 Shipwatch Circ.

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $701 to $3,465/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $698 to $1,830/night

    Phoenix Gulf Towers 908

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $687 to $1,176/night

    Mana Kai #412

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $680 to $1,479/night

    99 Compass Point Way South #407

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $668 to $2,676/night

    Makena Surf B305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $663 to $1,742/night

    Phoenix Gulf Towers 2104

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $662 to $1,222/night

    Alexander 1121

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    Pool Hot Tub
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $662 to $1,332/night

    Alexander 718

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    Pool Hot Tub
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $662 to $1,332/night

    Alexander 1421

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $662 to $1,332/night

    Alexander 521

    4 BedroomsBathroomsSleeps 11
    2 nights minstay
    Pool Hot Tub
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $662 to $1,222/night

    Alexander 1620

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    Pool Hot Tub
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $662 to $1,332/night

    Alexander 611

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $662 to $1,222/night

    Alexander 604

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    Pool Hot Tub
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $662 to $1,332/night

    Alexander 1419

    3 Bedrooms2.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $659 to $2,004/night

    Noelani 307

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $656 to $2,979/night

    Polo Beach Club 107

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $644 to $2,388/night

    367 Via Lido Soud

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $638 to $1,765/night

    Somerset 904, Marco Island Vacation Rental

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $632 to $2,485/night

    Breeze Away- 2525 Bienville Blvd

    5 BedroomsBathroomsSleeps 20
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $632 to $2,360/night

    Lemon Breeze- 2521 Bienville

    5 BedroomsBathroomsSleeps 25
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $621 to $1,116/night

    Kahana Sunset A7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $606 to $2,295/night

    Makena Surf A204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $604 to $1,068/night

    Kahana Village 13 Oceanview 3Bed/2Bath

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations